Stories involving men and women being spanked together seem to be rare and old ones are getting harder to find. The search engine to Google groups was seems to have been crippled years ago and lot of the original websites by spanking authors who use to post in the newsgroups have sadly closed down. I did, however, mange to find this old story by Wintermute for you to enjoy.
The Resort
The resort was set in the redwood trees and medows, with a view of the ocean.  The rooms where large and set in small groups in buildings scattered around the grounds.

Like most resorts of this kind, there was a pool and tennis courts, you could get a seaweed facial or a Shiatsu message.  But this resort offered services of a more private nature as well.  At the customers request, after the whole body message, a spanking would be administered, leaving a glow on the bottom in addition to the muscles. The resort had what they referred to as a "full disciplinary staff". Guests might hear the sound of a paddle being applied to the bare bottom of an exhibitionists, taking a spanking over a spanking horse in the garden, only partly shielded by a hedge.  For those with more private tastes, an appointment could be arranged with a staff disciplinarian of the customers choosing and the spanking would be administered in their room. 
Cimarron and Debbie had found out about the resort from friends.  It was the sort of place that did not advertise.  Walking through the garden after checking into their room they saw a woman wearing only a bra and a pair of sheer panties, bent over a spanking bench being paddled. 
The next day, in the late afternoon they were walking by the tennis courts.  They stopped and watched a tennis game.  A man and a woman were playing and another woman was sitting in the raised referee's chair.  The man scored a point by hitting the ball into the far corner and the referee called "match point".  The man and the woman went to the net, kissed and the referee got down from her chair.  She was wearing a pair of spandex bike shorts that showed off the round curve of her bottom and a tee shirt with the resorts name on it.  Her hair was in a pony tail, threaded through the back of a baseball cap. 
The tennis players moved to the side where the referee stood. Debbie and Cimmeron noticed that there was a spanking bench behind the referee's chair.  The woman tennis player drank from a bottle of water and wiped the sweat from her face with a towel.  She was wearing a short tennis skirt with a matching top.  She put the water bottle and the towel down and bent over a spanking bench.  As her male tennis partner watched, the referee fastened the young woman's hands with straps attached to the spanking bench.  The referee flipped up the woman's short pleated skirt and removed her tennis panties and the white bikini panties that were underneath.  She then fastened the woman's legs to the spanking bench.  Positioned this way, the womans bottom was pushed up, her thighs spread exposing lips of her vulva. The young woman's legs and thighs gleamed with sweat from the tennis game that she was about to pay the price for losing. 
The referee took a paddle down from where it hung on the back of the   chair.  She knelt down beside the bound womans head, caressing her hair.  The referee she said something to the woman that Debbie and Cimmeron could not hear.  The woman nodded her head.  The referee stood up and moved behind the woman, and brought the paddle down hard across the womans raised buttocks.  She gave a stroke ever few seconds, spanking the bound womans bottom and upper thighs.  It looked to Debbie and Cimmeron that the strokes were harder as the spanking progressed, as the woman started crying out with each stroke.  The referee spanked the tennis player's bottom and upper thighs until they were crimson. 
She hung the paddle back on it's hook and took down a spanking strap.  She caressed the womans bottom and said something again.  When the woman answered she raised the strap and brought it down hard across the bound woman's buttocks.  The referee spanked the woman more slowly this time, her body rocking forward slightly with each stroke. The man stroked his partner's hair while the she was spanked with the strap.  It looked like the woman was crying.  They counted twenty strokes before the spanking stopped.  The womans bottom was a deep crimson and lined with wide welts from the strap.  The referee unfastened the woman's arms and legs, speaking to her softly as her partner caressed her.  The woman got up from the spanking bench, rubbed her bottom and and wiped away some tears.  She winced slightly as she dressed, putting her white bikini panties and tennis panties back on.  The couple got their rackets, towels and water bottles and left the court with the referee.  The crimson blush on the woman's upper thighs could be seen under her tennis skirt as she walked away. 
The next day they returned to the tennis courts to watch another game, between another man and a woman.  A different woman was refereeing this game.  The woman player was very good and this time the man lost.  After the match he bent over the spanking bench to take his punishment.  His partner removed his shorts and bikini briefs while the referee fastened his arms to the bench.  The woman tennis player then fastened his legs to the bench.  She bent over and wispered in his ear while she caressed him between the legs.  The referee waited behind them, holding a rattan cane.  When the woman moved out of the way, the referee raised the cane and brought it down hard across the man's ass.  The cane left a dark red welt against his the pale skin of his lean muscled buttocks.  She caned him until his bottom and upper thighs were heavily lined with welts.  Then the referee exchanged the cane for a strap, while the woman tennis player caressed her partner between the legs, moving her fingers over his hard cock and his balls.  The woman tennis player moved aside to allow the referee to spank her partner with the strap.  The strap cracked loudly across his ass and his thighs and he cried out after each stroke. 
After watching the tennis court spankings they had very hard, very intense sex.  They had both asked for spankings along with their messages, but they both wanted more, the images of woman and the man being punished after losing their tennis matches fresh in their minds. As they were passing the front desk Debbie asked "Why don't we sign up for a spanking session?" 
Cimarron agreed and they went to the concierge desk.  Debbie told the woman at the desk what they were interested in.  "Have you had a spanking session here before?" she asked. 
"No", Debbie answered 
The concierge gave them a book of photos, with short paragraphs describing the kind of session each disciplinarian specialized in. One of the women was named Julie.  The paragraph said that one of Julie's specialties was governess style punishment spankings for "naughty boys and girls".  That made them both shiver.  "Is Julie available?", Cimarron asked. 
The concierge pulled out an appointment book, and turned to a page labeled "Julie".  "You're in luck.  Julie has a 'bedtime' session available tonight at 9:00.  Will that work?" 
The looked at each other and both swallowed mentally.  "Yes, that would be fine", she answered. 
The concierge pulled out three sheets of paper.  "I'll need you to fill out these forms.  On the first sheet you need to put your names and room number down, I'll fill in Julie's name and the appointment time.  The second sheet describes the kind of sessions that are available.  You will need to answer the questions on that page.  The last page is the concent form for the spanking.  You will both need to sign that. 
Debbie filled in their names and room numbers and gave the top sheet to the concierge who completed it and wrote their names and the time on Julie's page of the appointment book. 
On the second page was printed: 
The Resort has an experienced disciplinary staff that is available to provide spanking sessions. Several issues should be understood before signing up for a spanking session.
Spankings are administered on the bare buttocks or over sheer panties, depending on the spanking session. This allows the disciplinarian to properly gauge the effect of the spanking.
Although the sessions are intimate in nature the disciplinary staff does not provide any sexual services.
During the session the customer is expected to explicitly obey all requests from the disciplinarian and address them as Sir or Ma'am. Failure to address the disciplinarian properly during a session or to follow the disciplinarian's requests may result in extra punishment or an end to the session, at the disciplinarian's discression.
Spankings are painful and will result in soreness. Depending on the person and the severity of the spanking selected, there may be marking or brusing.
To help the disciplinarian give you a satisifying session, please indicate a level of severity that most suits you.
- Moderate
The spanking will consist of between sixty and eighty strokes given with the hand and a light or medium paddle, leaving the buttocks a deep pink and resulting in short term soreness. Extra punishment strokes will only be assigned after a warning has been given first. The spanking may be taken over sheer panties.
- Hard The disciplinary session will consist of between eighty and one hundred strokes, given with a paddle, strap and cane. No more than thirty storkes will be administred with the cane. No more than twenty strokes will be administered with the strap. Some extra punishment strokes may be assigned for disobedience or moving out of position. Punishment strokes will be administered with a paddle. The spanking will leave the buttocks red, with some mild brusing or welting. There may be some soreness the next day. The paddling may be taken over sheer panties. Strokes with the cane or strap will be administered on the bare bottom.
If a couple is spanked together, any extra punishment strokes earned by one person for disobedience, clenching or moving out of postion during a spanking will be administered to both.
- Severe
This is a punishment session that will consist of between one hundred twenty and one hundred and fifty strokes, administered with a paddle, strap, bath brush, cane or whip. At least forty strokes will be given with the cane and/or whip and a minimum of twenty strokes will be administred with a heavy punishment strap. Extra punishment strokes will be liberally assigned for any disobedience, clinching of the buttocks while being spanked or failure to maintain position. Punishment strokes will be administered with a cane or whip. The spanking will leave the buttocks and upper thighs lined with welts over a deep crimson blush. Brusing will be visible the next day and sitting will be uncomfortable. The client will take the spanking naked.
During a session, the client may request an end to the session, but once a severity level has been selected it cannot be changed.
Cimarron looked at her.  "What do you think?  Hard or severe?" 
Debbie looked down at the paper and then back up.  "Severe, I think.   What about you." 
"Yes, severe"
She checked the box next to "severe" and passed the sheet to the   concierge. 
"Are you sure that this is what you want?" asked the concierge.   "Julie is a beautiful, kind, warm, sweet girl.  I think that comes   across in her photo.  Some people don't think that Julie could   administer a severe spanking. From personal experience I can assure   you that if you ask for a severe spanking you will get a long hard   punishment session." 
"Yes", Debbie said, "that's what we want.  I'm glad that Julie can be   both warm and strict." 
"Ok.  You're down for 9:00.  An hour is scheduled for the session.   You need to be ready and wearing only panties.  If you change your   mind or want to change the severity of the session you can do so   anytime before 7:00." 
They thanked the concierge and left.  Talking to her about the   spanking and reading the descriptions made them both very hot, but   they did not want to make love until after Julie spanked them. 
Waiting was hard, as they both kept thinking about the spanking they   had coming.  They both wondered more than once whether they really   should have signed up for the "hard" session instead of the "severe"   session.  They both ate lightly that evening, and were back to their   room at 8:00.   
"Maybe we should get undressed", Debbie said nervously glancing at   the clock, which read 8:30.  They undressed to the panties, Cimarron   wearing only a pair of cotton bikini briefs and Debbie in a pair of   sheer string bikini panties.  She remembered that she would have   been allowed to keep her panties on when she was paddled if they had   selected "hard", instead of severe. 
Debbie went to the cabinet next to the clothes closet and opened the   double doors.  Hanging on the doors and in the back of the    cabinet were a variety of paddles, canes, whips, spanking straps, a   hair brush and a bath brush.  She looked at them thinking about how   each would feel applied to her bare bottom. 
At exactly 9:00 there was a knock on the door.  Cimarron opened the   door to find the tall dark haired woman from concierge's photo.  She   was wearing a tan trench coat, closed to her collarbone, her long   dark hair cascading over the shoulders of the coat.  He moved aside   to let her in. 
"Are you Debbie and Cimarron?" Julie asked.  When they answered yes,   Julie said "I always confirm names and room numbers.  One of the   disciplinarians once gave a severe spanking to the wrong person and   did not find out until it was over.  I'm Julie and I'll be your   disciplinarian this evening." 
Julie took off the coat and hung it on a hook near the door.  She was   wearing a black boned corset, giving her figure an hourglass shape, her   breasts pushed up by the top.  The corset flaired out above her   hips, emphasizing the small black lace string bikini panties she was   wearing and the garter belt, holding up a pair of seamed black   stockings that ended small feet inserted into black stilletto   heels. 
Julie sat on the couch, her legs tucked up under her.  "You are my   last clients for this evening, so I can take a little longer to get   to know you" she told them. 
At first they were both very nervous, intimidated by this beautiful   woman who had come to give them a spanking.  Julie started asking   them a little about themselves and in a few minutes they were at   ease with her.  She moved the topic to their experience with   spanking, asking if this was part of their relationship, who got   spanked and how hard spanking were given. 
"Its important that I know a bit about you and your background to   help me decide what kind of spanking you need."  Julie looked from   one of them to the other and said with a bit of sadness in her voice   "I'm afraid that you both need to be punished.  I'm going to have to   give you are very hard spanking." 
Julie did seem like a very nice sweet, even gentle girl and it   occured to Cimarron that Julie really might be sad that it would be   her job to punish them.  A spanking is supposed to hurt and they had   asked for a severe spanking. 
"I'm going to have to punish you, but I have some leeway in deciding   the severity of your punishment.  I'm going to have to give you   between one hundred-twenty and one hundred-fifty strokes.  Forty   with the cane or whip and twenty with the heavy punishment strap.   That leaves sixty to ninety strokes, plus any punishment strokes, at   my discression.  You are being punished, so the final decision is up   to me, but I would like to get your input. 
I think that you both need a spanking that leans toward the severe   side, so I think that one hundred-forty strokes would be   appropriate.  You will get a warm-up paddling of forty strokes over   my lap.  Then I'll bend you both over the end of the bed and give   you twenty storkes with the cane, followed by a thirty stroke   whipping with ten strokes across the thighs.  After you take the   whipping I'll give you the required twenty strokes with the heavy   spanking strap.  I'll finish your punishment back over my lap with   thirty strokes with the bath brush, the last ten given extra hard. 
I have to give you most of this spanking, but I can leave out the   whipping and add strokes with the cane and the bath brush if the   spanking is too severe. 
"No, Ma'am" Debbie said.  "I don't think that the punishment is too   severe" 
"Young man?", Julie asked. 
"No, Ma'am.  It's not too severe" 
"In that case, I think that its time to give you a spanking."  She   turned to Debbie.  "Do you need to go to the bathroom first, honey?" 
"No, Ma'am" 
"Come with me", Julie said as she walked into the bedroom.  They   followed her, Cimarron looking at Julie's bottom as she walked, her   buttocks moving under the sheer lace of her panties.  Julie went to the   cabinet of spanking implements, took down a ruler paddle,   went to the bed and sat down on the end.  "I'll start with you
Debbie.  Please take off your panties and lie across my lap". 
Debbie pulled her panties down to her thighs, letting them slip down   to her ankles and stepped out of them, leaving her naked when she   lay across Julie's lap. 
"I'm going to start with twenty strokes across your bottom and then   we'll give Cimarron his turn under the paddle." 
Cimarron stood to Julie's right side, watching as she paddled Debbie   with the thin paddle, bringing the paddle down across Debbies   buttocks every few seconds.  Debbies legs were slightly spread,   giving him a view of her pussy between her thighs.  When it was his   turn to take his panties off and like naked over Julie's lap, he   had a very stiff erection.  Julie ignored it as she settled him over   her right thigh. 
The pain of the first stroke of the paddle was a bit of a shock and   soon the smacks of the paddle across his bare buttocks took his mind   off his erection which was pressing against Julie's bare thigh. 
"You can get up now, honey", Julie told him.  He got up and Debbie   returned to Julie's lap to finish her paddling.  Julie was spanking   harder now and soon each stroke was eliciting a faint "ow" from   Debbie.  Her bottom was blushed a deep pink when it was Debbies   turn to watch as Julie's paddle redden Cimarron's bottom. 
After Julie finished paddling Cimarron's and he had gotten up   from her lap, she put the ruler paddle back in the spanking   implement cabinet and took out a rattan cane.  The cane was about   three feet long and 3/8 inch in thickness. 
Julie held one end of the cane in each hand, across her upper thighs.   "I want you both side by side over the end of the bed.  Please move   move those two ottomans to the end of the bed." Julie told them.   "Then put two pillows on the end of the bed, kneel on the ottoman   and lie over the end of the bed, with the pillows under your hips." 
Julie stood watching them as they moved the pillows and the ottoman.   When they were both bent over the end of the bed, Debbie on the left   and Cimmeron on the right, their bottoms pushed up by the pillow she   told them "I'm going to cane you now."  She moved to Debbie, patting   her right thigh "I want you to spread you legs a bit, honey.  Good   girl."  Bent over the end of the bed in such a submissive position   Debbie felt very exposed, her thighs spread showing her pussy, her   bottom pushed up, presented, waiting for the first stroke of cane. 
"You asked for a punishment session.  The paddling I just gave you   was a warm up.  Your punishment is going to start with twenty   strokes of the cane.  I'm going to cane you hard and it is going to   hurt.  You both need to stay in position, with your bottoms up and   your buttocks relaxed.  If there is any squirming or clenching of   your buttocks after a stroke, I'll have to give you both two extra   punishment strokes."   
Julie tapped the cane lightly across their buttocks "Bottoms up", she   told them.  Debbie raised her bottom a little higher.  She heard the   whistle of the cane and felt the first stroke burn across her   bottom.  Debbie's buttocks quivered a bit, but she stayed in   position and did not clench. 
A few seconds later Julie administered another stroke across   Cimmeron's bottom.  She alternated strokes between then, drawing the   cane behind her and whipping it forward fast and hard every few   seconds.  Each stroke left a red welt across buttocks that were   already reddened from the paddling.  Soon each stroke was followed   by a cry of pain. 
After giving them each ten strokes with the cane, Julie let them   catch their breath for a couple of minutes, before administering the   last set of ten strokes.  The curve of their buttocks where lined   with ten welts.  When she started caning them again she gave the   strokes lower, across the lower part of the cheeks and the upper   thighs.  Cimmeron was the first to squirm and clench after she gave   him a hard stroke across the upper thighs. 
Julie caressed his bottom.  "I know that it hurts honey, but you need   to stay still.  I'm going to have to add two extra punishment   strokes".  Debbie began to cry as the caning continued and both of   them clenched and squirmed under the painful cane strokes. 
"I'm going to have to punish you both for not staying still during   your spanking" she told them after she finished giving them the last   ten strokes.  "I want to see those bottoms raised while you wait for   your punishment." 
Julie returned the rattan cane to the spanking implement cabinet and   took out a black carbon fibre cane.  Julie used this cane to   administer extra punishment strokes because strokes from this cane   hurt more than those from the rattan cane.  When she moved back to   the couple she was happy to see their bottoms raised as she had   ordered.  Julie thought that Debbie looked lovely, her welted bottom   pushed up, her thighs spread exposing her pussy. 
Julie caressed the welts on Debbies bottom.  "I'm going to give you   each eight strokes with the punishment cane.  This time I will not   give you extra punishment for squirming or clenching, but I do   expect you to stay in position and take your spanking."  Julie drew   the cane back and brought it down hard across Cimmeron's upraised   ass.  Julie quickly followed with a stroke across Debbie's bottom.   She gave the strokes fast and hard and Debbie was crying when the   spanking was over. 
Julie went back to the cabinet and exchanged the black cane for a   spanking whip.  The whip looked like a riding crop, but where a   riding crop would have a flat leather slapper, the spanking whip   tappered down from the handle into a rod-like end.  She returned to   the end of the bed, where Debbie and Cimmeron waited for their   spanking to continue.  Their buttocks and upper thighs where crimson   and lined with darker red welts, which on Debbies bottom where   shading toward purple.  Julie caressed Debbie's bottom and thighs.   The skin was hot.  "Do you want to continue, honey" she asked. 
"Yes, Ma'am", Debbie answered.  "I've been a naughty girl and I need   to be punished." 
"Well then, I'm going to have to give you both a whipping", she told   them.  Even though they had asked for the spanking and they could   stop it if they wanted, Julie always felt some reluctance to inflict   the pain called for in a severe spanking.  But she reminded herself   that it was what they needed and it was her job to whip the soundly. 
"You will get thirty strokes with the whip, ten across the bottom,   followed by ten across the thighs and finally ten on the bottom.   The whipping is going to hurt, so I hope that you will remember the   lesson with the punishment cane and resist squirming and clenching   so I don't have to give you extra punishment strokes." 
Julie began whipping them.  The whip hurt as much as the cane, but   with a deeper more penitrating stroke.  Julie was pleased that they   both stayed still, although the both cried out after each stroke. 
Julie caressed their inner thighs with the tip of the whip.  "Put your   legs together so I can whip you across the thighs" she told them   after giving them the first ten strokes.  The whip strokes across   their thighs burned like hot metal and they both cried out as Julie    slowly whipped them.  The pain made the whipping seem to last a long   time.  When it was finally over, she told them to spread their   thighs again and she whipped them across the buttcks. 
After Julie finished whipping them, she sat down on the bed between   them.  She rubbed their backs and caressed their bottoms and thighs.   Debbie was crying, but stopped under Julie's caresses.  "You both   took your whipping very well.  I know that it hurt a lot and it was   hard to stay still."  Julie spent a few minutes rubbing their backs,   feeling them relax under her touch.  If she had to cause pain it was   nice to give comfort too. 
"Your spanking is almost over" she told them.  "I have to give you   twenty strokes with the punishment strap.  Then I'll take you each   over my knee and finish your spanking with the bath brush.  Can you   take that for me?" 
After they had both answered "Yes, Ma'am" Julie got up and put the   whip back in the cabinet and got the strap.  It was about two feet   long, with a wood handle attached to a heavy leather blade. 
"Lets get those bottoms up" Julie ordered.  Cimmeron heard the strap   crack loudly across across Debbie's upraised ass, followed by her   cry.  A few seconds later he felt the strap burn across his   buttocks.  The heavy punishment strap had a penitrating stroke which   rocked them forward slightly as they where spanked across the ass or   their thighs.  They were both very sore from the caning and the   whipping Julie had given them and they barely managed to stay still,   with their bottoms raised, as Julie punished them with the strap. 
After she finished strapping them, let the catch their breath for a   few minutes.  They both lay limp over the end of the bed as she put   the strap back and got the bath brush. 
"You can get up now", she told them.  Julie sat on the edge of the   bed, in the middle.  "Cimmeron, honey, please come over here.  I'll   take you over my knee first." 
Cimmeron went over to Julie's right side.  She patted her lap,   "Almost over honey, you just need to take a paddling over my knee   and it will be all over."  He lay across her lap.  Debbie watched as   Julie spanked Cimmeron with the brush, alternating cheeks.  When Julie   had given him twenty strokes on each side, she stopped for a few   minutes and let him rest.  "The last ten are going to be extra hard,   honey.  I want you to take your punishment for me and then it will   all be over."  Julie spanked him slowly and very hard as Debbie   watched, knowing that she would soon replace Cimmeron over Julie lap.
"You can get up, honey", Julie told Cimmeron.  Without being told,   Debbie lay over Julie's lap to take her spanking.  It brought back   memories of being a girl getting spanked on the bare bottom over her   mothers lap with the heavy ebony hairbrush her mother kept on her   dresser.  The paddling Julie gave her with the brush hurt exquisitely   and soon she was crying like a she had when she was a girl.  As Julie   gave her the last ten strokes on each cheek, very hard and slow,   memory fused with the present.  She was a girl again, with her   panties aroudn her knees and her dress pushed up.  As she cried   while Julie spanked her, she promised her mommy that she would be a   good girl.  When the spanking was over Julie held Debbie in her arms,   stroking her hair, telling her she was a good girl, until she   stopped crying. 
"You can put you panties on" Julie told them, as she handed Debbie   her panties which were lying on the bed.  Julie hugged them both and   told them that she was every proud of them for taking such a hard   spanking.   
"It has been a pleasure and an honor to be your disciplinarian and I   would be happy to spank you both again if you want another session."   Julie put her trench coat on, buttoning it to the neck, slipped into   her spike heels and left. 
As Cimmeron kissed Debbie he cupped her bottom in his hands.  Her   bottom was hot through the sheer material of her panties.  He   slipped his hand down the front of her panties, caressing her pussy,   which was very wet. 
"Will you do something for me, my love?" Debbie asked. 
"Yes, of course" 
"I want you to pile the pillows in the middle of the bed and lie   face down over them." 
As he did as she asked, she got a pair of sheepskin cuffs from the   cabinet. 
"Hold out your hands" Debbie ordered as she attached the cuffs.  She   clipped the rope from the cuffs to the head board.  She got two more   cuffs and removed his panties, attaching the cuffs to his ankles and   clipping them to the sides of the bed.  His bottom was pushed up by   the pillows, his legs spread.  He was totally helpless and she could   do to with him what she wanted. 
Debbie went to her bag and removed a silicone dildo, a condom, a dildo   harness and a tube of lube.  She put the condom on the dildo, put   the dildo through a hole in the harness and slipped the harness on.   The welts on her thighs hurt as she tightened the harness straps so   that the dildo was held firmly, pushing out from her mons. 
Debbie got a paddle from the cabinet and went to where Cimmeron lay   and knelt between high spread legs.  She caressed his bottom.    His   buttocks and thighs were still red and hot from the spankinig.  She   ran her fingers over the raised welts left by the cane, whip and   strap.  "Does you bottom hurt, my love". 
"Yes", he said, raising his bottom in response to her caress. 
"Spankings are supposed to hurt", she reminded him.  "But your   punishment is not over.  I'm going to finish punishing you by   raping you with the dildo.  I want you to be a good boy and take a   good hard fucking.  If I get any resistance, I'm going to have to   spank you." 
She put some lube on her right index finger and spread his buttocks   with her left hand.  He was helpless to move away from her probing   finger, but he tightened as she pushed her finger inside him. 
"Naughty boy!", she told him.   
She picked up the paddle and started spanking him, alternating   cheeks.  His bottom was very sore from the spanking Julie had given   him and each smack with the paddle elicited an "ow".  When Debbie had   given him ten strokes on each cheek, she put the paddle down.  "Have   you learned your lesson, naughty boy?  Are you going to take your   fucking like a good boy?" 
"Yes, Ma'am" he answered.
She put lube on her finger again and spread his cheeks.  This time   when she pushed her finger into his anus there was no resistance.   She put more lube on the dildo and guided the tip to his lubricated   anus.  Spreading his buttocks open with the fingers of each hand,   she pushed the dildo inside him.  She moved on top of him,   supporting herself on her arms, pushing the dildo deeper inside him   with her hips.  When she pushed the dildo all the way inside him,   she could feel his bottom, hot against her loins.  Debbie started   fucking him, using shallow strokes, pushing hard against his sore   bottom.  The dildo felt good as it pushed aganst her mons.  She   loved punishing him with the dildo, fucking him and the feeling his   hot freshly spanking ass beneath her. 
As she fucked him she wispered in his ear "Are you my boy?"  "Yes,   Ma'am" "Raise your ass and take it for me."  He raised his hips as   much as the cuffs allowed, taking the dildo a little deeper.  "You   like being raped up the ass, don't you nasty boy?"  "Oh, Yes Ma'am"
After fucking him for about five minutes she slowly withdrew the   dildo and took it out of the harness.  She unbuckled the cuffs on   Cimmeron's hands and ankles.  He got up and she moved the cuffs out   of the way and replaced him over the pillows, leaving the lub beside   her.  She reached back, cupping a buttock in each hand and spread   her cheeks, pushing her bottom up.  Cimmeron used his index finger   to put lube in her anus and then put more more lube on his cock.  He   started fucking her ass, moving just the tip of his cock in and out,   then gradually moving deeper.  She moved her right hand to her clit   and fingered herself as he fucked her.  She started to move against   him, pushing him deeper and he started to fuck her harder.  He also   loved the feel of her hot punished ass as he fucked her.  She came   first and he came a few seconds later.
When they went to breadfast the next morning they found that the   concierge had informed the breakfast staff that they would have two   sore bottomed guests and their chairs had thick pillows on them. 
 
